Process of making quinin carbonic ether.



llmrrnn STATES PATENT Orrrcn.

HEINRICH THRON, OF FRANKFORT-ON-THE-MAIN, GERMANY, ASSIGNOR TO VEREINIGTE CHININFABRIKEN, ZIMMER & 00., GESELLSOHAFT MIT BE- SOHRANKTER HAFTUNG, OF SAME PLACE.

PROCESS OF MAKING QUININ CARBONIC ETHER.

SPECIFICATION forming part of Letters Patent No. 640,977, dated January 9, 1900. Application filed November 28, 1899. Serial No. 738.571. (N0 specimens.)

ments in the process protected by the United States PatentNo. 585,068 of making qninin carbonic ether. According to this patent the said pharmaceutical products are made by acting upon thelevogyrate alkaloids of the cinchona-bark with derivatives of the chlorocarbonic acid. Now I have found that in this process the saidalkaloids can be replaced by their salts, which under circu mstancesare better obtainable than the alkaloids them selves. The method of procedure is to act on the alkaloidal salt, preferably in the anhydrous condition, with the particular derivative of chlorocarbonic acid either alone or dissolved in some suitable solvent.

Example I. Preparation ofthe chlorocarbom'c ether of qut'm'n 0r chlorocarbonyl qaiain-36.05 kilograms of anhydrous quinin hydrochlorid (two molecular proportions) are dissolved in two hundred kilograms of chloroform, and into the cooled solution there are passed 9. 9 kilograms of phosgene, (one molecular proporti0n,) which also can be in excess. The reaction proceeds according to the equation chlorocarbonic ether of quinin obtained in this way has the properties described in the specification of the aforesaid patent.

Example II. Preparation of qut'm'n carbonic ethyl ether.-36.05 kilograms of anhydrous qninin hydrochlorid (one molecular proportion) are suspended in one hundred and fifty kilograms of benzene and heated to boiling, while 10.85 kilograms of chloroformic ethyl ether (one molecular proportion) 01" even a small excess are allowed to flow slowly into the continuously-agitated liquid. The reaction proceeds according to the equation When the operation is complete, the benzene is distilled off, the residue dissolved in water,

the quinin carbonic ethyl ether produced being precipitated by means of alkali and recrystallized from dilute alcohol, when a small quantity of quinin which has escaped the ac tion of the chloroformic ether remainsin the motherliquor. action may be removed from the benzene so lution by agitation with wateror with dilute acid. Other anhydrous qninin salts-for example, 37.3 kilograms of anhydrous qninin sulfatemay be used in the place of quinin hydrochlorid. The quinin carbonic ethyl ether obtained in this wayhas the properties described in the specification of the aforesaid patent.

Example III. Preparation of gain in carbonic benzyl ether-36.1 kilograms of anhydrous quinin hydrochlorid are suspended in one hundred and fifty kilograms of benzene and treated with 17.1 kilograms of chloroformic benzyl ether, added gradually to the boiling liquid. When the reaction is complete, the benzene is distilled oif or the hydrochlorid quinin carbonic benzyl ether is extracted from it by agitation with water or a dilute acid. On adding an alkali the other is set free and may be recrystallized from dilute alcohol.

Quinin carbonic benzyl ether crystallizes in slender white needles which melt at 110 centigrade and dissolve readily in alcohol, ether, benzene, or chloroform.

I claim-- 1. The herein-described method of preparing pharmaceutical products by acting upon the salts of the alkaloids of the cinchona-bark Obviously the product of rewith derivatives of the chlorocarbonic acid, i In testimony whereof I have signed iny substantially as and for the purpose set forth.

2. The herein-described method of preparing pharmaceutical products by acting upon 5 the salts of the alkaloids of the cinchona-bark 1 Witnesses:

with an ether of chlorocarbonic acid, substan- RICHARD GUENTHER, tially as and for the purpose set forth. CARL GRUND.

name to this specification in the presence of two subscribing Witnesses.

HEINRICH THRON. 

